Steroid and cembranoids from the Dongsha atoll soft coral Lobophytum sarcophytoides
Journal
Tetrahedron
Journal Volume
66
Journal Issue
35
Pages
7129-7135
Date Issued
2010
Author(s)
Lu, Y.
Lin, Y.-C.
Wen, Z.-H.
Su, J.-H.
Sung, P.-J.
Hsu, C.-H.
Kuo, Y.-H.
Chiang, M.Y.
Sheu, J.-H.
Abstract
A novel sterol, sarcophytosterol (1), and four new cembranoids, sarcophytolins A-D (2-5), have been isolated from the soft coral Lobophytum sarcophytoides along with four known metabolites 6-9. The relative structures of new metabolites were elucidated on the basis of extensive spectroscopic analyses and X-ray diffraction analysis of 1, and the absolute configurations of 1 and 5 were determined by Mosher's method and CD spectrum, respectively. Compound 1 is a steroid possessing an unusual (20R,23R,24R)-23,24-dimethyl-20- hydroxy side chain. Compounds 3, 6, 8, and 9 were shown to exhibit cytotoxicity toward a limited panel of cancer cell lines. Furthermore, while 1 could effectively enhance the expression of the pro-inflammatory iNOS protein in LPS-stimulated RAW264.7 macrophage cells, compounds 2, 3, 5-7 and 9 were found to effectively inhibit the accumulation of the pro-inflammatory of iNOS. ? 2010 Elsevier Ltd.
Subjects
HBXZGJYKFRYIFQ-NBGGPTHLSA-N; IRLJYXHINXXWKC-GHZBUWTKSA-N; KBQKZBYGDQCBTJ-YQGAQXSRSA-N; OKPPSLJDJGOWAJ-UWVYSTBFSA-N; YQXSXPBPDWRFHK- LXIPXPQRSA-N
SDGs
Other Subjects
antiinflammatory agent; antineoplastic agent; cembranoid; cyclooxygenase 2; inducible nitric oxide synthase; lipopolysaccharide; sarcophytolin A; sarcophytolin B; sarcophytolin C; sarcophytolin D; sarcophytosterol; steroid; unclassified drug; antiinflammatory activity; antineoplastic activity; article; cancer cell culture; carbon nuclear magnetic resonance; circular dichroism; coral; crystal structure; cytotoxicity; drug isolation; drug mechanism; drug structure; human; human cell; Lobophytum sarcophytoides; macrophage; nuclear Overhauser effect; priority journal; protein expression; proton nuclear magnetic resonance; stereochemistry; X ray diffraction; Alcyonacea; Lobophytum
Type
journal article